Senior Delivery Operations & Enablement Director at Priceline

This role is eligible for our hybrid work model: 2 days in-office

Senior Delivery Operations & Enablement Director

Our Technology team is the backbone of our company: constantly creating, testing, learning and iterating to better meet the needs of our customers. If you thrive in a fast-paced, ideas-led environment, you’re in the right place.

Why This Job’s a Big Deal

The Senior Delivery Operations & Enablement Director is a senior operational leader accountable for optimizing the technology and product delivery operating model—driving excellence, consistency, and scalability across portfolios. This role defines the frameworks, insights, and enablement platforms that power the effectiveness of engineering and product teams.

This leader operates as a force multiplier—establishing the practices, data systems, and cultural habits that elevate delivery performance and developer experience across the enterprise. While not directly managing delivery teams, this role requires deep operational leadership, systems thinking, and strong influence across senior engineering, product, and finance stakeholders.

The ideal candidate brings expertise in production operating model design and optimization, with a track record of enabling tech and product organizations to deliver faster, more predictably, and with higher quality.

In This Role You Will Get To

Delivery Operating Model & Practices

• Define, evolve, and institutionalize the enterprise delivery operating model, integrating Agile, Lean Portfolio Management, and DevOps principles to create scalable, efficient execution patterns.
• Serve as the center of excellence for delivery methodologies, partnering with engineering, product, and portfolio leaders to ensure consistent application and maturity.
• Develop frameworks and toolkits to standardize portfolio governance, delivery planning, and measurement across teams.
• Partner with Developer Experience and Platform teams to define developer productivity and experience metrics aligned with industry benchmarks (e.g., DORA, SPACE frameworks).
• Drive continuous learning and maturity improvement through onboarding, playbooks, and targeted enablement programs.
  
  

Analytics, Insights, & Performance Management

• Define and operationalize delivery health and performance metrics (velocity, quality, predictability, capacity utilization, developer experience)
• Lead the design and rollout of dashboards and reporting systems that transform delivery data into executive and operational insights.
• Partner with Finance and Product to connect delivery performance to business outcomes—improving investment transparency and ROI tracking.
• Conduct developer experience research and benchmarking to identify systemic friction points and prioritize improvement investments.
  
  

Tooling & Enablement Platforms

• Own the roadmap and governance for delivery tooling ecosystems (e.g., JIRA, ADO, Confluence, analytics platforms).
• Drive tooling standardization and adoption, ensuring consistent workflows, data hygiene, and automation across portfolios.
• Partner with enterprise architecture and platform engineering to align tooling investments with productivity and operating model goals.
  
  

Influence, Leadership, & Change Enablement

• Operate as a trusted advisor to Technology and Product leadership, bringing data-driven insights and pragmatic recommendations.
• Lead change management efforts that drive adoption of new practices, tools, and performance systems across the organization.
• Foster a culture of transparency, accountability, and continuous improvement.
• Communicate insights and recommendations effectively to executives and portfolio leaders, connecting delivery performance to strategic business impact.
  
  

Who You Are

• 10+ years of experience in technology delivery, engineering operations, or large-scale product development.
• Proven experience designing and optimizing delivery operating models in scaled tech or digital organizations.
• Deep expertise in Agile, Lean Portfolio Management, and DevOps frameworks, with practical experience applying them across multi-team environments.
• Strong proficiency with delivery and productivity analytics tools (e.g., JIRA, ADO, Power BI/Tableau, developer productivity telemetry).
• Demonstrated ability to translate operational data into business insights and drive executive decision-making.
• Experience developing and implementing training, enablement, and maturity uplift programs for technical organizations.
• Excellent communication, facilitation, and influencing skills—comfortable engaging at all levels, from engineers to C-suite.
• Strategic mindset with strong operational rigor—able to move fluidly between conceptual design and execution.
• Illustrated history of living the values vital to Priceline: Customer, Innovation, Team, Accountability and Trust.
• The Right Results, the Right Way is not just a motto at Priceline; it’s a way of life. Unquestionable integrity and ethics is essential.
  
  

Preferred Attributes

• Experience standing up a delivery center of excellence in a scaled tech enterprise.
• Familiarity with engineering productivity frameworks (e.g., SPACE, DORA) and modern developer platforms.
• Proven success operationalizing cross-functional delivery measurement—bridging product, engineering, and finance.
• Background in consulting, technology strategy, or transformation leadership is a plus.
  
  

There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. In addition to a competitive base salary, certain roles may be eligible for an annual bonus and/or equity grant.

The salary range for this position is $200,000K- $250,000K USD.

Who We Are

WE ARE PRICELINE.

Our success as one of the biggest players in online travel is all thanks to our incredible, dedicated team of talented employees. Priceliners are focused on being the best travel deal makers in the world, motivated by our passion to help everyone experience the moments that matter most in their lives. Whether it’s a dream vacation, your cousin’s graduation, or your best friend’s wedding - we make travel affordable and accessible to our customers.

Our culture is unique and inspiring (that’s what our employees tell us). We’re a grown-up, startup. We deliver the excitement of a new venture, without the struggles and chaos that can come with a business that hasn’t stabilized.

We’re on the cutting edge of innovative technologies. We keep the customer at the center of all that we do. Our ability to meet their needs relies on the strength of a workforce as diverse as the customers we serve. We bring together employees from all walks of life and we are proud to provide the kind of inclusive environment that stimulates innovation, creativity and collaboration.

Priceline is part of the Booking Holdings, Inc. (Nasdaq: BKNG) family of companies, a highly profitable global online travel company with a market capitalization of over $80 billion. Our sister companies include Booking.com, BookingGo, Agoda, Kayak and OpenTable.

If you want to be part of something truly special, check us out!

Flexible work at Priceline

Priceline is following a hybrid working model, which includes two days onsite as determined by you and your manager (ideally selecting among Tuesday, Wednesday, or Thursday). On the remaining days, you can choose to be remote or in the office.

Inclusion is a Big Deal !

To be the best travel dealmakers in the world, we believe our team should reflect the broad range of customers and communities we serve. We are committed to cultivating a culture where all employees have the freedom to bring their individual perspectives, life experiences, and passion to work.

Priceline is a proud equal opportunity employer. We embrace and celebrate the unique lenses through which our employees see the world. We’d love for you to join us and help shape what makes our team extraordinary.

Applying for this position

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